Ethyl Acetate → HCID 67282556, compound

Participants

Reaction Conditions

Reaction Steps

5-(6-Aminopyridin-3-yl)-7-chloro-3-(2-chlorobenzyl)-1-(4-methoxybenzyl)-1H-benzo[e][1,4]diazepin-2(3H)-one was prepared following the procedure for the corresponding reaction in Example 12. 5-(6-Aminopyridin-3-yl)-7-chloro-3-(2-chlorobenzyl)-1-(4-methoxybenzyl)-1H-benzo[e][1,4]diazepin-2(3H)-one (175 mg, 0.33 mmol) was then dissolved in anhydrous anisole (4 mL), aluminum chloride (263 mg, 1.98 mmol) was added and the mixture was heated to 85° C. for one hour. The solution was cooled to ambient temperature, poured onto ice, and ethyl acetate added then slurried for 10 minutes. The layers were separated, and the aqueous layer extracted with ethyl acetate. The combined organic layers were washed with brine, dried with sodium sulfate, decanted and concentrated in vacuo. Column chromatography eluting with a gradient of 0-5% methanol in ethyl acetate provided 5-(6-aminopyridin-3-yl)-7-chloro-3-(2-chlorobenzyl)-1H-benzo[e][1,4]diazepin-2(3H)-one (113 mg, 83% yield). 1H NMR (300 MHz, d6-DMSO) δ 3.44 (m, 2H) 3.72 (m, 1H), 6.40 (m, 1H), 6.48 (s, 2H), 7.18-7.64 (m, 9H), 7.83 (m, 1H), 10.70 (s, 1H); ESI m/z measured 411.0783 [M+H]+. calculated 411.0779.

Provenance & Evidence